Jaime Derringer

Jaime Derringer is a phenomenal artist, entrepreneur, podcast host, and all-around creative. From design blogs with global reach of millions – to a curation of personal artwork that has been featured in magazines, TV shows, films, and even collected by celebrities – all the way to her most recent endeavor as an online retailer, Jaime’s unique ventures have certainly earned her great recognition in the entrepreneurial space. We chat with Jaime about her transition into entrepreneurship, learning to confront your need for creativity, and when necessary, to step away when encountered with self doubt.

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You’ve built quite an empire of successful projects over the years. From my understanding, this all started while you were shopping online for household items, and used a blog to bookmark things you liked? When did you realize there was potential in turning it into the success it is today?That’s correct. The first time I truly realized there was a business opportunity here was when someone contacted me and asked me if they could advertise on my website. A light bulb went off!

I’d love to learn more about your personal artwork. When and how did you begin to try your hands as an artist?I’ve been creative all my life, but always suppressed it for the “practical thing.” However, around 2006, I started drawing… mostly doodling. I enjoyed it so much that eventually, I started drawing more consistently and began using a sketchbook. I was very busy working on Design Milk between 2009 and 2011 and so I didn’t make much artwork. After my daughter was born in 2011, I really started to take it seriously. I decided to expand beyond pen and pencil and start trying my hand at paints and pastels on canvas. I’ve been painting and drawing every week, sometimes daily, since then. I find it to be mostly relaxing and stress relieving. However, there are times of frustration and self-doubt. Ultimately, I do feel like art has added a new dimension to my life. It’s helped me discover who I really am, giving me the confidence to be that person.

Thanks for sharing, Jaime. How have you found it best to deal with those times of frustration and self doubt in your work?Every artist or creative has moments of self-doubt and frustration. Sometimes, we have to push ourselves through it because of tight deadlines, but if you can allow yourself some time to step away, I would recommend doing that. There are times that I want to draw, but when I start to, it doesn’t go as well as I’d hoped. That tells me that I need to take some time away from it. Recharge my battery, in a sense. Forcing yourself to be creative isn’t ideal, even though there are times when we must do so… I like to take some time away from it and then come back to it when I feel a bit refreshed. Accepting the fact that you will be frustrated or doubtful is the first step!

“Sometimes, we have to push ourselves through it … but if you can allow yourself some time to step away, I would recommend doing that.

So all in the year of 2006, you started Design Milk and finally unleashed your creativity through drawings. It seems like there was a creative burst happening all at once for you. Did something spark, or do you think it was a natural result of having suppressed your creativity all those years?I have no idea why 2006 was a pivotal year for me. It’s bizarre that all of these creative births seemed to happen in that one year, but there was nothing specifically eventful or life-changing for me during that year. The only thing that I can think of that may have had an impact was that I had found a job I was fairly content with, and I finally felt a bit settled in my career. Previously, I had hopped around from job to job. I would not have left that job had I not moved to California in 2007; I liked it and enjoyed the work and my co-workers. I think that once I had mentally settled down, perhaps my brain decided it was OK to open up other doors and focus on other things. Sometimes, we mentally or emotionally run away or avoid things in our lives that need to be addressed. I think at that point in my life, I suppose I had avoided my need for creativity for long enough and the void revealed itself… I couldn’t run away from it any longer.

“I suppose I had avoided my need for creativity for long enough and the void revealed itself… I couldn’t run away from it any longer.

Can you also share about that leap into full-time entrepreneurship? Why did the option of creating your own path now outweigh the option of the “practical thing”?By that point, I hadn’t found any solace or happiness in going the practical route. I didn’t mind what I did for a living, but I didn’t love it and it didn’t feel like what I was supposed to be doing. There was a hunger and a need for something else/something more and I was unable to ignore it anymore. Of course, I didn’t leap into the unknown without first lining up my ducks: we made sure we were financially secure, ensured we had a support system, and determined that we would be OK in the long run. Then I took the leap of faith. We had eliminated most of the obstacles that would make it impractical for me to give it a go—that way, if it failed, we would still be alright. Quitting your job to follow your passion doesn’t happen in a vacuum, and it’s important that you recognize how it affects everyone around you, and anticipate obstacles… assessing risk and making informed decisions is something you need to do as a business owner anyway, so you’d better get started before you jump right in without a safety net.

“Quitting your job to follow your passion doesn’t happen in a vacuum, and it’s important that you recognize how it affects everyone around you

As if you weren’t already a wearer of many hats, I see you also launched an online jewelry shop sometime last year. Can you share a little more about it – perhaps your vision for the brand and the challenges faced thus far?Well, I’ve been buying designy jewelry for many years now and when out, especially at design trade shows and events, I was always asked where did I get it? It was hard for me to keep track, so I thought it would be a good idea to pull together some of the coolest modern jewelry and create a shop where I could tell people to go. There aren’t too many online stores dedicated to artistic jewelry, and I thought there needed to be one. Every product in the shop is hand picked by me.

The biggest challenge that I am facing is that I’m one person with a lot of other work to do, and therefore, I can’t dedicate 100% of my time to the shop. It’s frustrating because I want to give it more of my energy, but it’s also totally bootstrapped, so at the moment, I can only give it what I can… I’m also not an experienced retailer, and being an online shop requires lots of email marketing and targeting and SEO experience specifically dedicated to products. That’s not me, so I’m slowly learning what to do (and what not to do!). Ultimately, my goal is to expand the shop and do some in-person sales events and even bring in other accessories, not just jewelry.

Retailing definitely seems like a complex space. What have been some of those key takeaways on what to (and what not to) do? For one, you probably don’t want to do what I’m doing, which is to take it on as a side project! Retailing is a full-time job and should be treated as such. Also, marketing and promotion is very, very important – you have to create sales, change up your inventory, send lots of emails and constantly be putting up instagrams, tweets, Pinterest posts, and Facebook posts – it’s a lot of work! There is also a lot of research you should do on SEO, email marketing, and customer targeting. There is an art to selling products online, and I am no master at it.

What does a typical day look like for you? Working as hard as you do, I’m sure there’s some form of a structure to maintain a healthy lifestyle. I live by my routine. I am a creature of habits, so my days are mostly planned out. I don’t travel as much as I used to and so I’ve become even more reliant on my routine. Now that I have a kid, too, routine has become critical in our home to maintain our sanity! I love working in my home office. I’m most productive in there, sitting at my computer. I have a hard time focusing elsewhere – too many distractions!

My days are so boring, honestly. Take the kid to school, work, work, work, exercise, eat, work, work, work, work, Netflix, draw, sleep. Ha. I’m a night person, not a morning person, so I tend to do a lot of catching up on social media and with friends/life in the evening. I’m very focused on work during the day. I rarely even go out for lunch!

The web is certainly a very noisy place, and is only becoming more so. How do you think an aspiring blogger should go about cutting through that noise in 2017? These days, I might actually advise against starting a blog. I think it’s more important to analyze one’s goals and decide what might be the best path to achieve them. However, if someone definitely wants to blog, that’s awesome! I would suggest taking some time to explore what kind of message you want to send. The blogosphere is crowded and full of me-toos, so the best advice I can give is to position yourself in a different way than others: find what sets you apart and follow that path.